EMPLOYMENT AGREEMENT

EMPLOYMENT AGREEMENT

THIS EMPLOYMENT AGREEMENT (the “Agreement”) is entered into by and between Matthew Pittinsky (“you”) and Blackboard Inc. (“Blackboard”).

WHEREAS, Blackboard desires to continue to employ you on the terms and conditions hereinafter set forth and you desire to accept such employment;

NOW, THEREFORE, in consideration of the promises and the mutual agreements contained herein, the parties agree as follows:

1. Responsibilities. Blackboard agrees to continue to employ you as the Chairman. You shall devote your entire business time, attention, skill and energy exclusively to the business of Blackboard and perform the responsibilities assigned to you in accordance with the standards and policies that Blackboard may from time to time establish. You may engage in appropriate civic or charitable activities and devote a reasonable amount of time to private investments or boards or other activities provided that such activities do not interfere or conflict with your responsibilities and are not or are not likely to be contrary to Blackboard’s interests. You and Blackboard agree that your position is essential to Blackboard’s success and that the highest level of performance is required from you. For the avoidance of doubt, this Agreement applies only to your role as an employee of Blackboard and not to your membership or position on Blackboard’s Board of Directors (the “Board”).

2. Term of Employment. Blackboard agrees to employ you, and you agree to remain in employment with Blackboard, from November 14, 2005 until November 14, 2009 (the “Initial Term”), unless your employment terminates earlier pursuant to Section 5 below. This Agreement shall automatically renew for successive one (1) year periods (each, a “Renewal Term” and together with the Initial Term, the “Term”) unless either party provides prior written notice of its intent not to renew within thirty (30) days of the applicable Renewal Term.

3. Compensation.

(a) Base Compensation. Your annual base compensation shall initially be US$245,000 (“Base Compensation”), less applicable taxes and withholdings, payable in accordance with Blackboard’s regular payroll practices from time to time in effect. The Boardmay review and adjust your Base Compensation periodically.

(b) Bonus Compensation. To be eligible to receive an annual bonus for any year, you must meet financial performance targets set by the Board and be employed through March 31^st of the following year. Your target bonus during the initial year of this Agreement shall be 50% of your Base Compensation. The actual amount of the bonus, if any, will be determined by the Board in its sole discretion (the “Bonus”). If a Bonus is awarded, it will be paid in the year following that for which the Bonus is being awarded. You will receive your Bonus for the initial year of this Agreement, if any, in fiscal year 2006 for fiscal year 2005.

(c) Business Expenses. During the Term, Blackboard shall pay or reimburse you for all ordinary and reasonable business-related expenses you incur in the performance of your duties under this Agreement. Blackboard will reimburse you for all such expenses upon the presentation by you of an itemized account of such expenditures, together with supporting receipts and other appropriate documentation.

4. Employee Benefits.

(a) In General. During the Term, you shall be eligible for all employee benefits that Blackboard may provide to employees who are officers of Blackboard, which may include, but are not limited to benefits such as health insurance plans, a stock option plan, paid holidays and 401(k), subject in each case to the generally applicable terms and conditions of any such plan or program in question and to the determinations of any person or committee administering any such plan or program. Blackboard reserves the right to modify or terminate any such benefit at any time.

(b) Vacation. You shall be eligible to take paid vacation during each calendar year in accordance with Blackboard’s Employment Handbook.

5. Termination of Employment. Upon the effective date of termination of your employment with Blackboard (the “Termination Date”), you will not be eligible for further compensation, benefits or perquisites under Sections 3 and 4 of this Agreement, other than those that have already accrued or vested as of the Termination Date. Termination of your employment may occur under any of the following circumstances:

(a) Expiration of Term. Your employment will terminate if the Term provided for under Section 2 expires pursuant to the notice requirements of Section 2; or

(b) Termination of Employment by Blackboard. Blackboard has the right to terminate your employment at any time with or without Cause. For all purposes under this Agreement, (“Cause”) shall mean:

(i) non-feasance or your material breach of this Agreement, provided that Blackboard first provides you with written notice of such failure and you fail to cure it within ten (10) days of such notice;

(ii) an act or omission by you that constitutes gross misconduct, moral turpitude or fraud;

(iv) a material breach of any legally recognized duty owed to Blackboard (e.g., your duty of loyalty and confidentiality); or

(c) Resignation by You. You have the right to resign your employment with Blackboard at any time, with or without Good Reason, provided that you may resign with Good Reason only if you provide notice of such reason for resignation to Blackboard stating that such reason will be grounds for resignation with Good Reason, and if Blackboard fails to cure such reason within thirty (30) days following receipt of such notice.

(i) For purposes of this Agreement, “Good Reason” shall mean (A) a material failure by Blackboard to perform its obligations under this Agreement; (B) your relocation outside of your current residential area without your consent; or (C) a material diminution of your compensation or status at any time or for any reason other than for Cause during the Term of this Agreement. Notwithstanding the foregoing, you agree that a change of your current role to the position of Chief Executive Officer, Chief Education Officer, Chief Strategy Officer or Vice-Chairman of Blackboard shall not be deemed to be a material diminution of your status under Section 5(c)(i)(C).

(ii) During the Term, you agree to provide Blackboard ninety (90) days’ prior written notice of your resignation, with or without Good Reason. Blackboard may in its sole discretion place you on paid administrative leave as of any date prior to the end of such ninety (90) day notice period and request that you no longer be present on Blackboard premises. During any period of paid administrative leave, you will not be authorized to act as a representative, or make any statements on behalf of, Blackboard; or

(d) Death or Disability. Your employment shall be deemed to have been terminated by you upon your (i) death or (ii) inability to perform your duties under this Agreement, even with reasonable accommodation, for more than twenty-six (26) weeks, whether or not consecutive, in any twelve-month period (“Disability”). Termination will be effective upon the occurrence of such event.

6. Severance Benefits.

(a) If, during the Term of this Agreement, Blackboard terminates your employment without Cause (as defined in Section 5(b)) or if you terminate your employment with Good Reason (as defined in Section 5(c)), then Blackboard will pay you $750,000 (“Severance Payment”). The Severance Payment shall be less applicable taxes and withholdings. To receive the Severance Payment you must sign a release of any and all claims in the form provided by Blackboard. The Severance Payment shall be made in one lump sum, unless otherwise agreed by you and Blackboard, at the later of (i) the first pay period following your Termination Date or (ii) ten (10) days after you deliver the signed release.

7. Return of Property. Upon termination of your employment with Blackboard for any reason, you agree to immediately return to Blackboard all equipment, credit cards and other property belonging to Blackboard. This includes all documents and other information prepared by you or on your behalf or provided to you in connection with performing your duties for Blackboard, regardless of the form in which such documents or information are maintained or stored, including computer, typed, written, imaged, audio, video, micro-fiche, electronic or any other means of recording or storing documents or other information. You hereby warrant that you will not retain in any form any such document or other information or copies thereof, except as provided in the following sentence. You may retain a copy of any documents describing any rights or obligations you may have after the Termination Date under any employee benefit plan or other agreements.

8. Confidentiality, Non-Solicitation and Non-Competition Agreement.

(a) Confidential Information. You shall not disclose or use at any time, either during your employment or after your Termination Date, any confidential information, including, but not limited to, the terms of this Agreement, existing and prospective investments, trade secrets or proprietary information, strategic sourcing information or analysis, financing information and sources, patents, patent applications, developmental or experimental work, formulas, test data, prototypes, models, know how and product specifications, financial information, financial projections and pro forma financial information, sales and marketing strategies, plans and programs and product development information, employees’ and consultants’ benefits, perquisites, salaries, stock options, compensation, formulas or bonuses, and their non-business addresses and telephone numbers, organizational structure and reporting relationships, business plans, names, addresses, phone numbers of customers, contracts, including contracts with clients, suppliers, independent contractors or employees, business plans and forecasts, and existing and prospective projects or business opportunities (“Confidential Information”) of Blackboard, whether patentable or not, which you learn as a result of your employment with Blackboard, whether or not you developed such information. “Confidential Information” shall not include, without limitation, information that is or later becomes publicly available in a manner wholly unrelated to any breach of this Agreement by you as of the date it enters the public domain. If you are uncertain whether something is Confidential Information you should treat it as Confidential Information until you receive clarification from Blackboard that it is not Confidential Information. Confidential Information shall remain at all times the property of Blackboard. You may use or disclose Confidential Information only as authorized and necessary in performing your responsibilities under this Agreement during your employment with Blackboard; with the General Counsel’s prior written consent; in a legal proceeding between you and Blackboard to establish the rights of either party under this Agreement, provided that you stipulate to a protective order to prevent any unnecessary use or disclosure; or subject to a compulsory legal process that requires disclosure of such information, provided that you have complied with the following procedures to ensure that Blackboard has an adequate opportunity to protect its legal interests in preventing disclosure. Upon receipt of a subpoena that could possibly require disclosure of Confidential Information, you shall provide a copy of the compulsory process and complete information regarding the circumstances under which you received it to Blackboard by hand delivery within twenty-four (24) hours. You will not make any disclosure until the latest possible date for making such disclosure in accordance with the compulsory process (“Latest Possible Date”). If Blackboard seeks to prevent disclosure in accordance with the applicable legal procedures, and provides you with notice before the Latest Possible Date that it has initiated such procedures, you will not make disclosures of any Confidential Information that is the subject of such procedures, until such objections are withdrawn or ruled on. You hereby acknowledge that any breach of this Section 8(a) would cause Blackboard irreparable harm.

(b) Outside Activities. You shall submit to Blackboard’s General Counsel, within a reasonable time prior to dissemination, the text of any speech, professional paper, article or similar communication created by you which relates to Blackboard’s present or future business or research and development endeavors. The General Counsel then will notify you if the dissemination of the communication is permitted under the terms of this Agreement.

(c) Ownership of Confidential Information; Return of Materials. All Confidential Information, including without limitation that which is produced by or for Blackboard by you or anyone else, all materials embodying Confidential Information, and all copies thereof, will remain the property of Blackboard or of the third party who has furnished it to Blackboard. On your Termination Date, or at the written request of Blackboard at any time, you will immediately deliver to Blackboard all materials, and copies thereof, which are in your possession or control and which contain or are related in any way to any Confidential Information. This includes all documents and other information prepared by you or on your behalf or provided to you in connection with your duties while employed by Blackboard, regardless of the form in which such document or information are maintained or stored, including computer, typed, written, imaged, audio, video, micro-fiche, electronic or any other means of recording or storing documents or other information. You hereby warrant that you will not retain in any form any such document or other information or copies thereof. You may retain a copy of this Agreement and any other document or information describing any rights you may have after the termination of your employment.

(d) Intellectual Property.

(i) For purposes of this Agreement the following terms will be defined as indicated:

(A) “Inventions” shall mean inventions, ideas, formula, developments, designs, systems, software, discoveries, and improvements to existing technology, whether or not patentable.

(B) “Improvements” shall mean all inventions, developments, modifications, changes, whether or not patentable, made to any Inventions and/or Confidential Information.

(C) “Copyrighted Work” shall mean any work of authorship eligible for copyright protection under the federal and state laws of the United States and foreign countries.

(D) “Copyrights” shall mean any and all rights granted in Copyrighted Works under the laws of the United States and foreign countries.

(ii) Exclusions. An Invention, Copyright or Copyrighted Work will not be subject to this Agreement when all the following criteria are met: (A) no equipment, supplies, facilities, or Confidential Information of Blackboard was used in developing the Invention or Copyrighted Work or in applying for or obtaining a patent or Copyright; (B) the Invention or Copyrighted Work was developed entirely on your own time; (C) the Invention or Copyrighted Work does not relate directly to the business of Blackboard or to Blackboard’s actual or demonstrably anticipated research or development; and (D) the Invention, Copyright or Copyrighted Work does not result from any work performed by you for Blackboard or at the request of Blackboard.

(iii) Ownership and Assignment of Rights.

(A) All Inventions, Improvements, or Confidential Information that you have or will conceive or develop, either alone or with others, shall be the exclusive property of Blackboard. You hereby assign, and agree to assign, to Blackboard your entire right, title, and interest in and to (I) any and all such Improvements and Inventions, (II) any and all applications for patent, domestic and foreign that may be filed on said Improvements and Inventions, and (III) any and all patents that may issue or be granted on such applications, except those excluded under Section 8(d)(ii) of this Agreement. Both during and after your Termination Date you will on request immediately sign and deliver to Blackboard without further consideration any and all documents necessary to perfect the assignments granted in this Section.

(B) You understand and agree that all Copyrighted Works conceived, developed, created or contributed to by you shall be considered works made for hire under the copyright laws of the United States and shall be the exclusive property of Blackboard. Blackboard shall be considered the author of such Copyrighted Works. You further understand and agree that in the event any Copyrighted Work created by you within the scope of, or in connection with, your work with Blackboard, or at the request of Blackboard, fails to meet the legal requirements of a work made for hire owned by Blackboard, then this Agreement shall operate to assign to Blackboard all of your rights, title, and interest, including copyrights, in, to and under such Copyrighted Works. Blackboard shall have sole and absolute discretion to register, enforce, and/or assign Copyrights for such Copyrighted Works.

(iv) Assistance and Designation of Agent.

(A) Both during and after your Termination Date, you will on request immediately sign and deliver to Blackboard without further consideration, all instruments in writing requiring your signature and deemed by Blackboard to be necessary or advisable in, or in connection with, filing or prosecuting of any application for any patent covering Improvements, Inventions or any divisional, continuing, renewal or reissue application or reexamination request based upon any application for patent. In the event that Blackboard is unable for any reason whatsoever to secure your signature to any lawful and necessary documents required to apply for or execute any patent application with respect to such idea, process, development, design, system, program, discovery, invention, improvement or writing (including renewals, extensions, continuations, divisions or continuations in pat thereof), you hereby irrevocably designate and appoint Blackboard and its officers and agents, as your agents and attorneys-in-fact to act for and on your behalf and instead of you, to execute and file any such application and to do all other lawfully permitted acts to further the prosecution and issuance of patents thereon with the same legal force and effect as if executed by you.

(B) You will aid Blackboard promptly on request, and without further consideration, in any matter pertaining to or relating to the protection of any of the Improvements, Inventions, applications for patents covering Inventions or Improvements, and/or Copyrighted Works. If such request is made after your employment has ended, Blackboard will reimburse you for any expenses incurred and compensate for any services rendered in complying with such request at the same rate at which you were compensated during the final month of your employment.

9. Non-Solicitation/Non-Competition.

During your employment and for one (1) year following your Termination Date (the “Restricted Period”) you will not, except with prior written approval of Blackboard’s General Counsel, directly or indirectly, individually or as part of or on behalf of any other person, company, employer or other entity: (a) hire or attempt to solicit for hire, or encourage to end their relationship with Blackboard, any persons who have been employed by Blackboard at any time within the previous six (6) months (a “Covered Employee”); (b) sell or otherwise provide, or solicit for the purposes of selling or otherwise providing, services or products that are similar or related to those sold by Blackboard as of the Termination Date to any person or entity that has within the twelve (12) months preceding the Termination Date purchased any such services or products from Blackboard and with whom you had direct contact on behalf of Blackboard during that time; or (c) own, manage, operate, control, be employed by, participate in, work in, advise, consult or contract with, or support in any manner any business that is similar to the type of business conducted by Blackboard as of the Termination Date within the geographical area in which, as of the Termination Date, Blackboard is actively marketing or has made a significant investment in time and money to prepare to market its products or services within the six (6) month period after the Termination Date. You agree that these provisions are necessary to protect Blackboard’s legitimate business interests. You warrant that the provisions will not unreasonably interfere in your ability to earn a living or to pursue your occupation after the Termination Date. You agree to notify any person or entity to which you provide services during the Restricted Period of your obligations under this Section 9.

10. Non-Disparagement. You agree to refrain from making any derogatory or defamatory remarks or comments that may disparage Blackboard, or any officer, employee or agent of Blackboard during your employment or after your Termination Date.

11. Other Obligations. You warrant that you are not subject to any other obligations that would conflict with or inhibit your ability to perform your duties under this Agreement. You represent that you have disclosed to Blackboard the existence and contents of all covenants not to compete that you have entered into with any other entity. You further warrant that you have not and will not bring to Blackboard or use in the performance of your responsibilities at Blackboard any equipment, supplies, facility or trade secret information (that is not generally available to the public) of any current or former employer or organization other than Blackboard to which you provided services, unless you have obtained written authorization for their possession and use.

12. Miscellaneous Provisions.

(a) Notices. Unless otherwise provided herein, any notice or other communication required to be given under the terms of this Agreement must be in writing and must be personally delivered (i.e., left with an individual 18 years of age or older) or sent by overnight delivery. Documents sent by overnight delivery will be presumed received on the next business day following the day sent.

(b) Dispute Resolution. You and Blackboard agree that any dispute between you and Blackboard will be finally resolved by binding arbitration in the District of Columbia in accordance with the Federal Arbitration Act (“FAA”). You and Blackboard agree to follow the Dispute Resolution Procedures set forth in Attachment A to this Agreement.

(c) Nature of Agreement. This Agreement and the attachment hereto constitute the entire agreement between you and Blackboard and supercede all prior agreements and understandings between you and Blackboard relating to the matters covered by this Agreement, except for the existing stock option agreements between you and Blackboard, which remain in full force and effect. Any long-term equity incentives between Blackboard and you shall be contained in a separate agreement. In making this Agreement, the parties warrant that they did not rely on any representations or statements other than those contained in this Agreement. No modification of or amendment to this Agreement will be effective unless in writing and signed by Blackboard’s General Counsel. A delay or failure by Blackboard to exercise any right that is the subject of this Agreement will not be construed as a waiver of that right. A waiver of a breach on any one occasion will not be construed as a waiver of any other breach. Regardless of the choice of law provisions of the District of Columbia or any other jurisdiction, the parties agree that this Agreement shall be otherwise interpreted, enforced and governed by the laws of the District of Columbia. This Agreement will continue in effect until all obligations under it are fulfilled. If any part of this Agreement is held by a court of competent jurisdiction to be void or unenforceable, the remaining provisions shall continue with full force and effect. This Agreement is not assignable by you. This Agreement is binding on you with respect to Blackboard, its successors or assigns. This Agreement may be executed in any number of counterparts each of which shall be an original, but all of which together shall constitute one instrument. The headings in this Agreement are for convenience only and shall not effect the interpretation of this Agreement. You further certify that you fully understand the terms of this Agreement and have entered into it knowingly and voluntarily.

IN WITNESS WHEREOF, each of the parties has executed this Agreement, in the case of Blackboard by its authorized officer, as of the day and year set forth under their signatures below.

Blackboard Inc.